172138-95-3

Basic information

• Product Name: (+)-N,N'-(1S,2S)-1,2-DIAMINOCYCLOHEXANEDIYLBIS(2-PYRIDINECARBOXAMIDE)
• Synonyms: (+)-N,N'-(1S,2S)-1,2-Diaminocyclohexanediylbis(2-pyridinecarboxamide),min.98%;(+)-N,N''-(1S,2S)-1,2-DIAMINOCYCLOHEXANEDIYLBIS(2-PYRIDINECARBOXAMIDE), MIN. 98%;N-((1S,2S)-2-(picolinamido)cyclohexyl)picolinamide;(1S,2S)-N,Nμ-1,2-Cyclohexanediylbis(2-pyridinecarboxamide), (+)-N,Nμ-(1S,2S)-1,2-Diaminocyclohexanediylbis(2-pyridinecarboxamide), (1S,2S)-(+)-1,2-Bis[(2-pyridinylcarbonyl)amino]cyclohexane, (1S,2S)-1,2-Bis(2-pyridinecarboxamido)cyclohexane;(S,S)-DACH-pyridyl Trost ligand;(1R,2R)-(-)-1,2-Bis[(2-pyridinylcarbonyl)amino]cyclohexane;(1R,2R)-N,Nμ-1,2-Cyclohexanediylbis(2-pyridinecarboxamide), (1R,2R)-1,2-Bis(2-pyridinecarboxamido)cyclohexane;1S,2S- N,N’-1,2-Diaminocyclohexanediylbis (2-pyridinecarboxamide)
• CAS NO: 172138-95-3
• Molecular Formula: C₁₈H₂₀N₄O₂
• Molecular Weight: 324.38
• Product Categories: Chiral Nitrogen;DACH&Trost Series
• Mol File: 172138-95-3.mol
• Article Data: 6

Chemical Properties

• Melting Point: 170°C
• Boiling Point: 663.366 °C at 760 mmHg
• Flash Point: 354.991 °C
• Appearance: off-white/Powder
• Density: 1.255 g/cm³
• Storage Temp.: 2-8°C
• PKA: 12.51±0.40(Predicted)
• CAS DataBase Reference: (+)-N,N'-(1S,2S)-1,2-DIAMINOCYCLOHEXANEDIYLBIS(2-PYRIDINECARBOXAMIDE)(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-N,N'-(1S,2S)-1,2-DIAMINOCYCLOHEXANEDIYLBIS(2-PYRIDINECARBOXAMIDE)(172138-95-3)
• EPA Substance Registry System: (+)-N,N'-(1S,2S)-1,2-DIAMINOCYCLOHEXANEDIYLBIS(2-PYRIDINECARBOXAMIDE)(172138-95-3)

Safety Data

• Hazard Codes: Xn
• Statements: 36/37/38-22
• Safety Statements: 26-36/37/39-36/37
• WGK Germany: 3
• Hazardous Substances Data: 172138-95-3(Hazardous Substances Data)

Usage

Reactions

Ligands for Mo catalyzed asymmetric allylic substitutions. Especially useful for the synthesis of tertiary and quaternary stereocenters. Exclusive license for this technology acquired by ChiroTech and is protected by pending Stanford University patents. Dynamic kinetic asymmetric formation of tertiary and quaternary stereogenic centers

Uses

Trost Ligands for Asymmetric Allylic Alkylation

Upstream product

• 98-98-6 2-Picolinic acid 
• 21436-03-3 (S,S)-1,2-diaminocyclohexane 
• 65-85-0 benzoic acid 
• 2524-52-9 ethyl-2-picolinate 
• 201230-82-2 carbon monoxide 
• 57785-86-1 pyridin-2-yl tosylate 

Relevant articles and documents

Practical Synthesis of Chiral N,N'-Bis(2'-pyridinecarboxamide)-1,2-cyclohexane Ligands

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Lanthanum(III) triflate catalyzed direct amidation of esters

Lanthanum trifluoromethanesulfonate is an effective single-component catalyst for synthesizing a variety of amides directly from esters and amines under mild conditions. Highly selective amidation of esters and amines, as well as catalyst-controlled amidation of esters, demonstrated the effectiveness of the catalyst system.

Ex situ generation of stoichiometric and substoichiometric 12CO and 13CO and its efficient incorporation in palladium catalyzed aminocarbonylations

A new technique for the ex situ generation of carbon monoxide (CO) and its efficient incorporation in palladium catalyzed carbonylation reactions was achieved using a simple sealed two-chamber system. The ex situ generation of CO was derived by a palladium catalyzed decarbonylation of tertiary acid chlorides using a catalyst originating from Pd(dba)2 and P(tBu)3. Preliminary studies using pivaloyl chloride as the CO-precursor provided an alternative approach for the aminocarbonylation of 2-pyridyl tosylate derivatives using only 1.5 equiv of CO. Further design of the acid chloride CO-precursor led to the development of a new solid, stable, and easy to handle source of CO for chemical transformations. The synthesis of this CO-precursor also provided an entry point for the late installment of an isotopically carbon-labeled acid chloride for the subsequent release of gaseous [ 13C]CO. In combination with studies aimed toward application of CO as the limiting reagent, this method provided highly efficient palladium catalyzed aminocarbonylations with CO-incorporations up to 96%. The ex situ generated CO and the two-chamber system were tested in the synthesis of several compounds of pharmaceutical interest and all of them were labeled as their [ 13C]carbonyl counterparts in good to excellent yields based on limiting CO. Finally, palladium catalyzed decarbonylation at room temperature also allowed for a successful double carbonylation. This new protocol provides a facile and clean source of gaseous CO, which is safely handled and stored. Furthermore, since the CO is generated ex situ, excellent functional group tolerance is secured in the carbonylation chamber. Finally, CO is only generated and released in minute amounts, hence, eliminating the need for specialized equipment such as CO-detectors and equipment for running high pressure reactions.